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Photocycloaddition of arylcarbothioamides with unsaturated systems. Synthesis of 3,5-diaryl-1,2,4-thiadiazoles and 3-aryl-4,4,5,5-tetramethylisothiazolines via photogenerated nitrile sulfides

✍ Scribed by Minoru Machida; Kazuaki Oda; Yuichi Kanaoka

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 140 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99897-6

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✦ Synopsis

On irradiation arylcarbothioamides (l_) undergo, in the absence of oxygen, the Paterno-BUchi reaction with olefins followed by cleavage, whereas under aerobic conditions the photoreaction proceeds to give 4 and 5 probably via nitrile sulfide intermediates. Although the photochemistry of thione has been extensively studied, 2) few reports have dealt with the photochemical properties of thioamides: namely, thiobenzanilides 3) and 4-thio-

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